Water → HCID 59837355, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(3-{4-[4-(morpholin-4-ylcarbonyl)tetrahydro-2H-pyran-4-yl]phenoxy}propyl)morpholine (160 mg, 0.38 mmol) in THF (4 mL) at 0° C. was added dropwise a solution of LiAlH4 (1.0M solution in Et2O, 1.15 mL, 1.15 mmol). The reaction mixture was stirred at 0° C. for 20 mins then heated at reflux for 1.5 hours. The reaction was then cooled to 0° C., water (0.10 ml) was added dropwise followed by sodium hydroxide (2.0M, 0.10 ml) and water (0.30 ml). The mixture was filtered through a short pad of celite, eluting with 1% methanol in dichloromethane (15 ml) and the organic washings concentrated in vacuo. The crude compound was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:ammonia, 97:3:0.3 to 92:8:0.8, to give the title compound as a clear oil (125 mg, 81%). 1H NMR (400 MHz, CDCl3) δ 1.83 (m, 2H), 1.95 (m, 2H), 2.07-2.16 (m, 6H), 2.40 (s, 2H), 2.43-2.50 (m, 4H), 2.52 (t, 2H), 3.51 (m, 6H), 3.76 (m, 6H), 4.01 (t, 2H), 6.82 (d, 2H), 7.21 (d, 2H). HRMS ESI+ m/z 405.2742 [MH]+.

Provenance & Evidence